Heteroatom-Doped Nanographenes with Structural Precision

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  • Xiao-Ye Wang
    State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China
  • Xuelin Yao
    Max Planck Institute for Polymer Research, Ackermannweg 10, 55128 Mainz, Germany
  • Akimitsu Narita
    Max Planck Institute for Polymer Research, Ackermannweg 10, 55128 Mainz, Germany
  • Klaus Müllen
    Max Planck Institute for Polymer Research, Ackermannweg 10, 55128 Mainz, Germany

書誌事項

公開日
2019-09-03
権利情報
  • http://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html
DOI
  • 10.1021/acs.accounts.9b00322
公開者
American Chemical Society (ACS)

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説明

Nanographenes, which are defined as nanoscale (1-100 nm) graphene cutouts, include quasi-one-dimensional graphene nanoribbons (GNRs) and quasi-zero-dimensional graphene quantum dots (GQDs). Polycyclic aromatic hydrocarbons (PAHs) larger than 1 nm can be viewed as GQDs with atomically precise molecular structures and can thus be termed nanographene molecules. As a result of quantum confinement, nanographenes are promising for next-generation semiconductor applications with finite band gaps, a significant advantage compared with gapless two-dimensional graphene. Similar to the atomic doping strategy in inorganic semiconductors, incorporation of heteroatoms into nanographenes is a viable way to tune their optical, electronic, catalytic, and magnetic properties. Such properties are highly dependent not only on the molecular size and edge structure but also on the heteroatom type, doping position, and concentration. Therefore, reliable synthetic methods are required to precisely control these structural features. In this regard, bottom-up organic synthesis provides an indispensable way to achieve structurally well-defined heteroatom-doped nanographenes. Polycyclic heteroaromatic compounds have attracted great attention of organic chemists for decades. Research in this direction has been further promoted by modern interest in supramolecular chemistry and organic electronics. The rise of graphene in the 21st century has endowed large polycyclic heteroaromatic compounds with a new role as model systems for heteroatom-doped graphene. Heteroatom-doped nanographene molecules are in their own right promising materials for photonic, optoelectronic, and spintronic applications because of the extended π conjugation. Despite the significant advances in polycyclic heteroaromatic compounds, heteroatom-doped nanographene molecules with sizes of over 1 nm and their relevant GNRs are still scarce. In this Account, we describe the synthesis and properties of large heteroatom-doped nanographenes, mainly summarizing relevant advances in our group in the past decade. We first present several examples of heteroatom doping based on the prototypical nanographene molecule, i.e., hexa-

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